An extraordinary castle-like estate in Connecticut is bringing a dash of old-world opulence to one of the state’s most upscale neighborhoods—lending a rare sense of regal elegance to an area already famous for its over-the-top mansions.
Known as Loch Lane Manor, the striking stone residence has nearly doubled in price since it last changed hands in 2020 for $6.9 million, recently returning to the market for the lofty price of $13.5 million.
Set on 3.22 acres, the custom-built manor is located at the heart of a picture-perfect parcel in Greenwich, CT, an extremely pricey suburb where the median list price currently sits at $3.3 million, nearly eight times the national median of $429,500.
But even in a place where luxury seems to seep from every perfectly manicured blade of grass and every immaculately placed brick, Loch Lane stands apart from the crowd, combining old-world European grandeur with modern luxury across more than 11,000 square feet of living space.
At first glance, the home’s storybook architecture, with its stone facade, oculus windows, and handsome turrets, creates the impression of a centuries-old manor. Sweeping lawns and meticulously curated gardens only enhance the feeling of having stumbled upon the residence of European royalty.
An extraordinary castle-like estate in Connecticut is bringing a dash of old-world opulence to one of the state’s most upscale neighborhoods—lending a rare sense of regal elegance to an area already famous for its over-the-top mansions. (Modern Media LLC )A gourmet kitchen features an oversized island and a very modern aesthetic. (Modern Media LLC )The dining room showcases the home’s blend of timeless and modern design. (Modern Media LLC )Natural light floods the interiors, including in all of the home’s many living room spaces. (Modern Media LLC )
The effect is entirely intentional. Custom-built in 2010, the six-bedroom estate includes a main residence, guest cottage, and pool house, all designed to to capture the charm and grandeur of a historic property.
“The residence, pool house, and guest cottage are unified by their handsome stone construction and slate roofs, a testament to a level of craftsmanship seldom achieved today,” says listing agent Leslie McElwreath.
According to McElwreath, the property would be nearly impossible to reproduce today, at least not for an attainable price, largely because of the soaring cost of materials—including the beautiful stone that covers so much of the estate’s exterior.
“In the current building environment, the cost of reproducing an estate of this quality and substance would far exceed its acquisition cost,” the listing agent notes.
Inside, custom millwork, soaring ceilings, and elegant formal spaces create an atmosphere that’s grand and welcoming. Large windows, white walls, and carefully curated finishes create a surprisingly bright and contemporary aesthetic that feels fresh rather than formal.
A terrace that stretches the length of the home serves as a natural extension of these spaces.
There is an office space located inside one of the home’s towers. (Modern Media LLC )The pool house was recently upgraded with a kitchenette. (Modern Media LLC )The grounds include mature specimen plantings, curated gardens, and even raised garden beds. (Modern Media LLC )
“The expansive rear terrace spans the length of the home and is designed as a true outdoor destination, complete with a built-in fireplace and multiple areas for relaxation and entertaining,” says McElwreath.
“With direct access from all of the principal rooms on the ground floor, the terrace becomes an integral part of the home’s gracious lifestyle.”
Beyond the terrace, beautifully landscaped grounds unfold around a resort-style swimming pool and pool house. Recent enhancements have further elevated the property’s appeal.
According to McElwreath, the current owners upgraded the pool house with a kitchenette, and also refinished the lower level of the main house to include a gym, media room, bar, and additional recreation spaces.
Despite its private setting, the estate is conveniently positioned near downtown Greenwich, with quick access to North Street’s boutiques and restaurants.
“Perfectly situated for today’s lifestyle, the home offers the tranquility of a private cul-de-sac setting without sacrificing convenience,” says McElwreath. “This is a property that delivers a breadth of amenities rarely found in a single offering.”
The enormous abode, which is known as Casa Encantada, was once home to financier Gary Winnick, who purchased the 8.5-acre estate for $94 million in 2000. At the time, it was one of the priciest home sales on record in the U.S.
However, after Winnick’s death in 2023, the home’s once-illustrious history became embroiled in a much murkier tale, when it was revealed in November 2025 that the property was slated to be sold off in a foreclosure auction the following month.
According to the Wall Street Journal, the foreclosure auction stemmed from a $100 million loan that was taken out by an entity tied to Winnick and his wife, Karen Winnick, in 2020.
By 2025, the lender, real estate investment firm CIM Group, alleged that repayments on the loan had ceased—and ordered that Winnick’s Los Angeles home, as well as another property in Malibu, be auctioned off to satisfy the debt, which it said had reached $150 million.
However, Winnick’s widow, Karen, later launched legal action against the firm, insisting that she was entirely unaware of the terms of the loan—and accusing CIM Group of concealing information, financial elder abuse, and transfer of property without spousal consent.
Now, it appears that Karen has been given another opportunity to offload the mansion herself, with records showing that it was relisted for $170 million on April 27. Though still an extraordinary price, it is $80 million below the original ask of $250 million in 2023.
And while $170 million is certainly nothing to scoff at, it is less than half the asking price of another nearby Los Angeles estate, which has hit the market for the eye-watering price of $400 million, rocketing to the top of the week’s most expensive homes list—while also becoming the priciest residential property to have ever been listed in the U.S.
Built in 2018, “The Crown Jewel” was designed by architect Peter Marino and took a decade to complete. Perched atop an 7.86-acre promontory overlooking the Bel-Air Country Club, the resort-inspired estate offers breathtaking views from the downtown skyline to the Pacific Ocean.
“No expense was spared in the design or construction of this global masterpiece,” the listing states. The primary residence boasts 10 bedrooms, 13 staff bedrooms, and wellness and fitness amenities “that rival the world’s finest destinations.”
It also has a six-bedroom guesthouse, which has an additional 10 staff bedrooms.
More over-the-top amenities include indoor and outdoor pools, a spa, meditation room, nail salon, screening room, fitness center, library, billiard room, and wine cellar.
More jaw-dropping estates to make the week’s most expensive homes list include a stone estate in Greenwich overlooking Long Island Sound, an oceanfront Florida mansion currently under construction on Golden Beach, and another massive Los Angeles estate also overlooking Bel-Air Country Club.
Fryman Canyon farmhouse: This stylish seven-bedroom mansion replaced the former home of late “Jeopardy!” host Alex Trebek.
Developers Mark Alexander and Rob Diaz purchased the 1.47-acre property for $8 million in 2022 to build this megamansion. The 17,627-square-foot estate debuted on the market for $42 million in September 2025.
A “Scandifornian”-style interior features two matching A-frames enveloped by stunning canyon views. Vaulted ceilings, glass walls, custom wood details, built-ins, a bunk room, two fireplaces, and an “Aman-inspired” spa with steam, cold plunge, sauna, and fitness center can be found throughout the home’s open floor plan.
Multiple lounge areas overlook an in-ground saltwater pool and spa.
Branden Williams of The Beverly Hills Estates Inc. is the listing agent.
Fryman Canyon farmhouse in Studio City, CA (Realtor.com)
Custom-designed mansion: This New England–style estate was built in 2023 and sits on a lushly landscaped acre of privacy.
An 11,746-square-foot modern floor plan features radiant oak floors, bespoke millwork, designer lighting, and an elevator. A two-story living room boasts a floor-to-ceiling fireplace and access to the outdoor living area. The spacious dining room designed for grand-scale entertaining has beautiful garden views. Other highlights include a first-floor primary wing, two offices, a lower-level entertainment area with wine cellar, lounge, bar, fitness center, steam room, and sauna. There is also a detached guesthouse for extended family and friends.
Three terraces with fireplaces overlook the pool, spa, and outdoor kitchen.
Ken Deleon of Deleon Realty is the listing agent.
Custom-built mansion in Atherton, CA (Realtor.com)
Brentwood Park: This five-bedroom mansion completed in 2023 took five years to build and features custom details, including steel doors and windows, hand-applied plaster walls, and disappearing pocket doors.
The 13,077-square-foot mansion also has a living room that opens to the private backyard, a formal dining room for entertaining, a fully-equipped gourmet kitchen, and a separate chef’s kitchen. There is also a wood-clad library/office with bar, a home theater, entertainment room, wine cellar, fitness center, and spa.
A loggia with an outdoor dining room and private terraces offers views of the pool and courtyard gardens.
Kurt Rappaport of Westside Estate Agency is the listing agent.
Port Royal: This five-bedroom waterfront mansion offers 147 feet “along one of the area’s deepest yacht basins” with a private dock.
Designed for the ultimate boating enthusiast, the nearly 1-acre property has no-wake bayfront views. Built in 1998, the modernized 6,883-square-foot interior features hardwood floors, expansive glass, custom built-ins, and vaulted ceilings. Other highlights include a home office, media room, modern kitchen, and primary suite with private covered terrace. A four-car garage has lift capabilities.
According to the listing, “Owners are eligible for membership to the exclusive Port Royal Club and Cutlass Cove Beach Club.”
William Earls of John R. Wood Properties is the listing agent.
Under construction: This 10-bedroom modern mansion in the exclusive Landmark Ranch Estates enclave is scheduled to be completed this month.
The “ultraluxury” residence created by RCR Homes boasts an ornate 23,977-square-foot interior with 14-foot ceilings, custom Italian cabinetry, designer lighting, and a sculptural floating staircase. A chef’s kitchen has a full butler’s kitchen with high-end appliances. A primary suite has a private lounge and terrace overlooking the pool. There is also a 20-car auto showroom.
Covered dining and sitting areas overlook the pool, spa, and summer kitchen.
Marc Brandt of Douglas Elliman is the listing agent.
New mansion in Southwest Ranches, FL (Realtor.com)
Long Island Sound views: This six-bedroom waterfront estate on 1.6 acres features sweeping coastal views and originally hit the market for $57,995,000 in August 2023.
The 12,492-square-foot rebuilt mansion features a barrel-vaulted great room, a chef’s kitchen with a marble breakfast bar, a water-facing dining room, a wood-clad lounge, and a home office with built-ins. A lavish upstairs primary wing has a steam shower, sauna, boutique-inspired closets, and a private balcony. Other luxurious amenities include a sauna, wine storage system, and fitness center.
A heated pool, private beach, deep-water dock, and protected cove for swimming and boating can also be found on property.
Jesse Marinak of Serhant Connecticut LLC is the listing agent.
Brand-new build: This seven-bedroom oceanfront estate is currently under construction and slated to be complete in 90 days, according to the listing.
Offering 50 feet of ocean frontage overlooking the Atlantic Ocean, the residence boasts floor-to-ceiling glass walls, a great room with fireplace, a dining room with wine storage, a chef’s kitchen with custom Italian cabinetry, and a primary suite with soaking tub, custom closets, and waterfront terrace. Covered terraces overlook the swimming pool with sundeck.
Located in the guard-gated Golden Beach enclave, the property includes a three-car garage and private beach access.
Pablo Umansky of Urban Group Realty Corp. is the listing agent.
Brentwood Circle: Hollywood producer Joel Silver is once again said to be trying to part ways with this eight-bedroom mansion that originally hit the market in 2020 for $77,500,000.
Located in a guard-gated enclave, the 25,000-square-foot home designed by architect Ricardo Legorreta is seamlessly integrated with the outdoor living area.
The “architectural masterpiece” boasts an open formal dining room, dual primary suites with marble bathrooms, a library, home office, fitness center, and a “one-of-a-kind” screening room. A reflection pool, outdoor heated dining, motor court, and four-car garage can also be found on the 4.56-acre lot.
The reduced price appears to have finally snagged a buyer, as the listing notes “the property is under contract.”
Branden Williams of The Beverly Hills Estates Inc. is the listing agent.
Casa Encantada: Perched atop an 8.4-acre promontory, this seven-bedroom mansion offering breathtaking views of Bel-Air Country Club originally hit the market for $250 million in 2023.
Last fall, it was slated to be sold in a foreclosure auction after the death of its longtime owner, financier Gary Winnick, who purchased the grand estate with his wife, Karen Winnick, for $94 million in 2000.
Built in 1937 and reimagined “in the grand Deco-Hollywood tradition,” the 28,725-square-foot interior boasts an oval foyer, sweeping staircase, grand hall with a 14-foot ceiling, formal and junior dining rooms, a walnut-paneled library, and dual living salons. An opulent primary suite has two sitting rooms, dual marble bathrooms, and dressing rooms.
The spacious lot features terraced rose gardens, botanical sanctuaries, orchard and herb gardens, a 60-foot tiled pool, tennis pavilion, sport court, and 15-car garage.
Jimmy Heckenberg of Rodeo Realty is the listing agent.
The ‘Crown Jewel’ of Los Angeles: This ultraluxurious 39-bedroom legacy compound on 7.86 acres boasts a jaw-dropping 70,000 square feet of lavish living space.
Built in 2018, the compound took a decade to complete and features interiors designed by Peter Marino. Lavish amenities include a 10-bedroom primary estate with 13 staff bedrooms, a six-bedroom guesthouse with 10 additional staff bedrooms, a media room, fitness center, library, wine cellar, billiard room, spa, and beauty salon.
Fountains, indoor and outdoor pools, a pool house, sport court with viewing pavilion, and four-car subterranean garage can also be found on the sprawling lot.
Jack Harris of The Beverly Hills Estates Inc. is the listing agent.
America’s most expensive home in Los Angeles, CA (Realtor.com)
